The Truth Behind The “Side Hustle”–Debunking The Myths Around Hustle Culture & Mapping The Road to…


If you’re considering doing your own thing or breaking into the gig economy, I have one thing that you need to know.

You will never feel lonelier than you will when you try to break into the world of freelancing.

You’ll feel exhilarated.

You’ll feel exhausted.

You’ll feel scared out of your mind.

And your head will hit the pillow every night feeling the immense satisfaction and responsibility of carrying your business on top of your own two shoulders.

We know that the internet has glamourized get-rich-quick schemes and the very best “versions” of things that we “should” be doing–which has led to an influx of people looking to break into the field, write or design a few things, and make it big.

That’s not how it works.

If you want to succeed in the world of entrepreneurship and business, you have to get your head in the game.

You have to be prepared for the inevitable ebbs and flows of your confidence.

You have to be prepared to ruthlessly defend your spot in the ring.

You have to be prepared to relentlessly seek knowledge, get humbled, and do it all again the next day.

It’s so much more than a TikTok about a new side hustle or creating your profile on Fiverr.

Those things are great starts, but it isn’t the essence of entrepreneurship, nor is it what makes you successful.

You make yourself successful. And you do that by keeping your mindset aligned with what success looks like for you at that moment.

I’ve had to learn a lot of hard lessons in my business ownership experience, which I’ve distilled down into five simple concepts that can help you to set yourself up for success:

  1. You will never be ready. Jump. (With caution). You will never be ready for your next opportunity. You won’t be ready to abandon your 9-to-5 and dive in full time. You will never be ready for your first revision request, your first business failure, or your first contract cancellation. You know why? Because you weren’t meant to. Your business offers you the privilege of making more complex failures, learning more complex lessons, and taking more complex risks. Go into the ring being excited to fail, learn, and scale, and watch how your landscape changes. I promise you won’t regret it.
  2. Don’t try to crush the curve in your first month. (Or year). Yep, hope is great. So are goals. But if you continue to pull 18-hour days at the expense of your mental health, family, and physical wellbeing, you will be putting yourself into the very same hole that caused you to jump into freelancing in the first place.
  3. Be your own advocate and create your own opportunities. (Always). Opportunities and leads don’t come to you. Ruthlessly chase them in a way that positively impacts your customer and caters to the “what’s in it for me” (WIIFM) motivation. Ditch the “Interested” Facebook comments, come up with some price lists and sample portfolios, and develop your pitch. Go to them, and add value wherever you go.
  4. Connect and network. (You don’t have competition). I am firmly convinced that there is no such thing as competition in freelancing. A rising tide lifts all boats–and you can network, refer, and help others thrive while staying in your own lane and finding your own successes. The road is lonely enough–you’ll benefit from some good-natured networking.
  5. Don’t forget why you did this in the first place. (Realign yourself regularly). Don’t get lost in the grind. Constantly bring your focus back to what put you here, and where you want to be. Balance and iterate accordingly–and don’t be afraid to turn it all on its head if it isn’t working for you.

Freelancing and entrepreneurship aren’t highlight reels. They’re lifestyles. You have to commit to the bit if you want to succeed, in whatever capacity you can–so determine what that looks like today to help you to take a step forward tomorrow.

I promise you–although the truth about freelancing and entrepreneurship is “scary,” “amazing,” and altogether-un-Pinterest-worthy, you’ll never regret the chances that you took to make a spot for yourself in your industry.

Like what you see? Give me a visit over at my LinkedIn, or like and share this post. I would love to be able to connect with you personally, too. Drop me a line at [email protected]